US7309590B2 - Method for producing an aqueous acrylamide solution with a biocatalyst - Google Patents

Method for producing an aqueous acrylamide solution with a biocatalyst Download PDF

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Publication number
US7309590B2
US7309590B2 US10/475,100 US47510004A US7309590B2 US 7309590 B2 US7309590 B2 US 7309590B2 US 47510004 A US47510004 A US 47510004A US 7309590 B2 US7309590 B2 US 7309590B2
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acrylonitrile
reaction
reactor
heat exchanger
mixture
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US20040175809A1 (en
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Olaf Petersen
Burkhard Theis
Michael Colberg
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Solenis Technologies LP USA
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Ashland Licensing and Intellectual Property LLC
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Priority claimed from PCT/EP2002/004567 external-priority patent/WO2002088373A2/de
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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12M—APPARATUS FOR ENZYMOLOGY OR MICROBIOLOGY; APPARATUS FOR CULTURING MICROORGANISMS FOR PRODUCING BIOMASS, FOR GROWING CELLS OR FOR OBTAINING FERMENTATION OR METABOLIC PRODUCTS, i.e. BIOREACTORS OR FERMENTERS
    • C12M47/00—Means for after-treatment of the produced biomass or of the fermentation or metabolic products, e.g. storage of biomass
    • C12M47/02—Separating microorganisms from the culture medium; Concentration of biomass

Definitions

  • the present invention relates to a method and a device for producing an aqueous acrylamide solution by hydrating acrylonitrile in an aqueous solution in the presence of a biocatalyst.
  • the object of this invention to provide a method in which the biocatalyst is damaged as little as possible during the reaction, by-products are minimised and the batch time is optimised.
  • the object is achieved by a method for producing an aqueous acrylamide solution by hydrating acrylonitrile in an aqueous solution in the presence of a biocatalyst during which the reaction mixture is mixed, the reactor comprising a pumping circuit in which a part of the reaction mixture is circulated by means of a pump and in which at least one heat exchanger is arranged.
  • the concentration of the biomass, expressed as solids is preferably 0.03-2.5 g/l, particularly preferably 0.05-1 g/l and the pH value is preferably 6.0-8.0, particularly preferably 6.5-7.5.
  • an agitating element with an intensive action is arranged in the reactor with which the reactor content is homogenously mixed.
  • the reactor comprises external half-pipe coils with which the reaction mixture can be additionally cooled during the conversion of acrylonitrile into acrylamide.
  • the reactor has a pumping circuit in which a part of the reaction mixture is circulated by means of a pump.
  • a pumping circuit in which a part of the reaction mixture is circulated by means of a pump.
  • Arranged in this pumping circuit is at least one heat exchanger with which the reaction heat may be drawn off.
  • the heat exchanger is a shell-and-tube heat exchanger in which advantageously the reaction mixture is not diverted in order to avoid fouling on the heat exchanger surfaces.
  • the pump and the heat exchanger(s) are designed to ensure the avoidance of, on the one hand, temperature fluctuations in the reactor and, on the other, excessive energy input from the pump.
  • the pump is a magnetically coupled side channel pump.
  • the addition of the acrylonitrile to the pumping circuit is very particularly preferably performed directly before the re-entry of the reaction mixture into the reactor.
  • the addition is preferably performed continuously.
  • a frequency-controlled piston-diaphragm pump has been found to be particularly advantageous as the feed pump for the acrylonitrile.
  • the course of the reaction in the reactor is advantageously monitored by means of on-line measurement.
  • This measurement enables the performance of the reaction to be adapted very quickly in response to any possible changes.
  • the on-line measurement is performed in the pumping circuit before the acrylonitrile feed point and preferably, the acrylonitrile and/or the acrylamide concentration are continuously monitored.
  • the results of the on-line measurement may be used to control the conversion.
  • the quantity of acrylonitrile added, the volume of the pumped flow, the bypass volume and the secondary reaction time are controlled.
  • the method according to invention may be performed with any biocatalyst that catalyses the conversion of acrylonitrile into acrylamide.
  • the biocatalyst is a Rhodococcus rhodochrous depsited under the deposition number 14230 with DSMZ, Deutsche Sammlung von Mikroorganismen und Zellkulturen GmbH (German Collection of Microorganisms and Cell Cultures Ltd), Mascheroder Weg 1b, D-38124 Braunschweig, Germany.
  • the method according to the invention has the advantage that during the conversion of acrylonitrile into acrylamide, the biocatalyst is damaged as little as possible and therefore the quantity of biocatalyst to be used is minimised, fewer by-products are produced, the conversion of the acrylonitrile takes place at least almost completely and that an acrylamide solution of up to 50% by weight is achievable.
  • the method according to the invention is simple and inexpensive to perform.
  • the method according to the invention enables the reaction times to be drastically reduced.
  • the biocatalyst is utilised to the optimum extent.
  • the method according to the invention is preferably performed in a device for the production of an aqueous acrylamide solution by hydrating acrylonitrile in an aqueous solution in the presence of a biocatalyst with a reactor, a pumping circuit in which a part of the reaction mixture is circulated by a pump and at least one heat exchanger arranged in the pumping circuit. Therefore, this device is a further subject of this invention.
  • an agitating element with an intensive action is arranged in the reactor with which the content of the reactor is homogeneously mixed.
  • the reactor comprises external half-pipe coils with which the reaction mixture may be additionally cooled during the conversion of acrylonitrile into acrylamide.
  • the reactor has a pumping circuit in which a part of the reaction mixture is circulated by means of a pump.
  • a pumping circuit in which a part of the reaction mixture is circulated by means of a pump.
  • Arranged in this pumping circuit is at least one heat exchanger with which the reaction heat may be drawn off.
  • the heat exchanger is a shell-and-tube heat exchanger in which the reaction mixture is advantageously not diverted in order to prevent fouling on the surfaces of the heat exchanger.
  • the pump and heat exchanger(s) are embodied to ensure the avoidance of, on the one hand, temperature fluctuations in the reactor and, on the other, excessive energy input from the pump.
  • the pump is a side channel pump.
  • the acrylonitrile is added to the pumping circuit directly before the re-entry of the reaction mixture into the reactor.
  • the addition is preferably performed continuously.
  • a frequency-controlled piston-diaphragm pump has been found to be particularly advantageous as the feed pump for the acrylonitrile.
  • a secondary reaction of preferably 4 to 20 minutes, particularly preferably 5 to 10 minutes, is required to convert the acrylonitrile as completely as possible.
  • the cooling it is advantageous for the cooling to be successively reduced with at least one bypass.
  • the course of the reaction in the reactor is advantageously monitored by means of an on-line measurement.
  • This measurement enables the performance of the reaction to be adapted very quickly in response to any possible changes.
  • the on-line measurement is performed in the pumping circuit before the acrylonitrile feed point and preferably, the acrylonitrile and/or the acrylamide concentration are continuously monitored.
  • the results of the on-line measurement may be used to control the conversion.
  • the quantity of acrylonitrile added, the volume of the pumped flow, the bypass volume and the secondary reaction time are controlled.
  • the device according to the invention has the advantage that during the conversion of acrylonitrile into acrylamide, the biocatalyst is damaged as little as possible and therefore the quantity of biocatalyst to be used is minimised, fewer by-products are produced, the conversion of the acrylonitrile takes place at least almost completely and that an acrylamide solution of up to 50% by weight is achievable.
  • the device according to the invention is simple and inexpensive to operate.
  • the method according to the invention enables the reaction times to be drastically reduced.
  • the biocatalyst is utilised to the optimum extent.
  • FIG. 1 is a schematic diagram of the method according to the invention or parts of the device according to the invention.
  • deionised water 1 and a suspension 2 containing the biocatalyst, are placed in the reactor 3 .
  • the content of the reactor 3 is mixed homogenously with a motor-driven agitator 16 .
  • On the exterior of the reactor 3 there are cooling coils 17 which are connected to the cold water inlet 5 and the cold water outlet 4 .
  • these cooling coils can also be used to heat the reactor content to a specific temperature before the start of the actual reaction.
  • the reactor 3 comprises a pumping circuit 18 through which a part of the reactor content is circulated by means of the magnetically coupled side channel pump 7 .
  • a pumping circuit 18 Arranged in the pumping circuit 18 are three shell-and-tube heat exchangers 6 connected in parallel with which the reactor content may be heated or cooled. The heat exchangers 6 are also connected in series to the cold water inlet or outlet.
  • the pumping circuit comprises the bypass 15 with which the heat exchanger 6 may be bypassed. The corresponding valves are not shown.
  • the pumping circuit also contains the Fourier transform infrared device (FT-IR device) 9 for the on-line measurement of the acrylonitrile and acrylamide concentration in the circulated flow 18 and hence in the reactor 3 .
  • FT-IR device Fourier transform infrared device
  • the sample flow is taken from the pumping circuit 18 and sent by means of the piston-diaphragm pump 8 to the FT-IR device 9 where it is analysed.
  • the analytical data are used to control the method.
  • the acrylonitrile to be converted is added thereto from the acrylonitrile receiver 10 by means of the diaphragm-feed pump 11 .
  • the acrylonitrile receiver 10 and the reactor 3 are connected to each other by means of a pendulum line 19 at the gas side.
  • the line 19 is opened before the addition of the acrylonitrile commences and closed again when the addition is completed.
  • the aqueous acrylamide is separated from the biomass by means of an annular gap centrifuge 12 and the aqueous acrylamide collected in the receiver 13 and the biomass in the receiver 14 .

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biotechnology (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Sustainable Development (AREA)
  • Biomedical Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Apparatus Associated With Microorganisms And Enzymes (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
US10/475,100 2001-04-26 2002-04-25 Method for producing an aqueous acrylamide solution with a biocatalyst Expired - Lifetime US7309590B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10120550A DE10120550A1 (de) 2001-04-26 2001-04-26 Verfahren zur Herstellung einer wässrigen Acrylamidlösung mit einem Biokatalysator
DE10120250.3 2001-04-26
PCT/EP2002/004567 WO2002088373A2 (de) 2001-04-26 2002-04-25 Verfahren zur herstellung einer wässrigen acrylamidlösung mit einem biokatalysator

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US20040175809A1 US20040175809A1 (en) 2004-09-09
US7309590B2 true US7309590B2 (en) 2007-12-18

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US (1) US7309590B2 (de)
EP (1) EP1385972B1 (de)
JP (1) JP4246499B2 (de)
KR (1) KR100973860B1 (de)
CN (1) CN100523207C (de)
AT (1) ATE410519T1 (de)
AU (1) AU2002302574B2 (de)
BG (1) BG66496B1 (de)
BR (1) BR0209237B1 (de)
DE (2) DE10120550A1 (de)
MX (1) MX265933B (de)
RU (1) RU2317976C2 (de)
ZA (1) ZA200308319B (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080108770A1 (en) * 2005-01-07 2008-05-08 Dia-Nitrix Co., Ltd. Process For Producing Amide Compound And Acrylamide Polymer
US8980588B2 (en) 2009-12-25 2015-03-17 Mitsubishi Rayon Co., Ltd. Method for producing acrylamide using microbial catalyst

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EP1689861B1 (de) * 2003-12-02 2011-11-09 Ciba Specialty Chemicals Water Treatments Limited Stamm von rhodococcus rhodochrous ncimb 41164 sowie dessen verwendung als nitrilhydrataseproduzent
CN100364657C (zh) * 2004-12-16 2008-01-30 劳关明 带有独立加热及冷却装置的反应锅
JPWO2007097292A1 (ja) * 2006-02-24 2009-07-16 三井化学株式会社 （メタ）アクリルアミドの製造方法
EP2336346B1 (de) * 2008-10-03 2016-12-07 Dia-Nitrix Co., Ltd. Verfahren zur herstellung von acrylamid
CN101665445B (zh) * 2009-09-14 2013-06-12 郑州正力聚合物科技有限公司 制备丙烯酰胺水剂的***及丙烯酰胺水剂的制备方法
RU2444512C1 (ru) * 2010-10-18 2012-03-10 Учреждение Российской академии наук Институт проблем химико-энергетических технологий Сибирского отделения РАН (ИПХЭТ СО РАН) Способ получения дигидрохлорида 2,7-бис-[2-(диэтиламино)этокси]-флуоренона-9
US9181569B2 (en) 2011-05-31 2015-11-10 Mitsubishi Rayon Co., Ltd. Method for producing acrylamide
CN103571898A (zh) * 2012-07-27 2014-02-12 上海市农药研究所 利用管壳式反应器的微生物催化生产丙烯酰胺的工艺和装置
JP6149731B2 (ja) * 2012-12-10 2017-06-21 三菱ケミカル株式会社 アクリルアミドの製造方法
CN103361268A (zh) * 2013-08-06 2013-10-23 宁波先安化工有限公司 丙烯酰胺连续催化水合制备***及其制备方法
KR20170066471A (ko) * 2014-09-30 2017-06-14 바스프 에스이 낮은 아크릴산 농도를 갖는 아크릴아미드 수용액의 제조 방법
AR113386A1 (es) 2017-10-25 2020-04-29 Basf Se Proceso y planta modular y reubicable para producir soluciones acuosas de poliacrilamida
AR113377A1 (es) 2017-10-25 2020-04-22 Basf Se Proceso para producir soluciones acuosas de poliacrilamida
AR113387A1 (es) 2017-10-25 2020-04-29 Basf Se Proceso y planta modular y reubicable para producir soluciones acuosas de poliacrilamida
WO2019081004A1 (en) 2017-10-25 2019-05-02 Basf Se PROCESS FOR PRODUCING AQUEOUS POLYACRYLAMIDE SOLUTIONS
WO2019081318A1 (en) 2017-10-25 2019-05-02 Basf Se PROCESS FOR PRODUCING AQUEOUS POLYACRYLAMIDE SOLUTIONS
WO2019081003A1 (en) 2017-10-25 2019-05-02 Basf Se PROCESS FOR PRODUCING AQUEOUS POLYACRYLAMIDE SOLUTIONS
WO2019081008A1 (en) * 2017-10-25 2019-05-02 Basf Se PROCESS FOR PRODUCING AQUEOUS ACRYLAMIDE SOLUTION
WO2020079119A1 (en) 2018-10-18 2020-04-23 Basf Se Method of providing aqueous polyacrylamide concentrates
WO2020079124A1 (en) 2018-10-18 2020-04-23 Basf Se Process for producing aqueous polyacrylamide compositions
CA3112658A1 (en) 2018-10-18 2020-04-23 Basf Se Process of fracturing subterranean formations
AR116742A1 (es) 2018-10-18 2021-06-09 Basf Se Proceso para producir un concentrado acuoso de poliacrilamida
CN109609368A (zh) * 2018-11-28 2019-04-12 浙江鑫甬生物化工股份有限公司 生物转化法生产丙烯酰胺的水合釜外循环进料冷却装置
MX2022005430A (es) 2019-11-05 2022-05-26 Basf Se Metodo de almacenamiento de un biocatalizador.
WO2021138205A1 (en) * 2019-12-30 2021-07-08 Kemira Oyj Ftnir spectroscopy for reaction monitoring of acrylamide synthesis
CN112266866A (zh) * 2020-10-27 2021-01-26 广东宝莫生物化工有限公司 一种丙烯酰胺生产***
WO2023041515A2 (en) 2021-09-15 2023-03-23 Basf Se Method for preparing an aqueous (meth) acrylamide solution

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Publication number Priority date Publication date Assignee Title
US4181576A (en) 1977-03-29 1980-01-01 Phillips Petroleum Company Fermentation method
DE3017005A1 (de) 1979-05-02 1981-04-09 Nitto Chemical Industry Co., Ltd., Tokyo Verfahren zur kontinuierlichen Herstellung von Acrylamid oder Methycrylamid aus Acryl-Nitril oder Methacrylnitril unter Verwendung von Mikroorganismen
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EP1385972A2 (de) 2004-02-04
DE50212867D1 (de) 2008-11-20
JP2004524047A (ja) 2004-08-12
BR0209237A (pt) 2004-06-08
JP4246499B2 (ja) 2009-04-02
CN100523207C (zh) 2009-08-05
ATE410519T1 (de) 2008-10-15
DE10120550A1 (de) 2002-10-31
BR0209237B1 (pt) 2013-06-18
KR20040014514A (ko) 2004-02-14
EP1385972B1 (de) 2008-10-08
KR100973860B1 (ko) 2010-08-04
AU2002302574B2 (en) 2008-02-28
WO2002088373A8 (de) 2002-12-05
WO2002088373A3 (de) 2003-01-30
ZA200308319B (en) 2004-10-25
US20040175809A1 (en) 2004-09-09
MX265933B (es) 2009-04-13
BG66496B1 (bg) 2015-06-30
CN1531597A (zh) 2004-09-22
RU2003133139A (ru) 2005-04-20

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